Efficient one-pot Ugi-Smiles couplings are reported for the use of furyl-substituted aldehyde components. In the presence of these heterocyclic aldehydes, reactions tolerated variations in amine components and led to either isolated N-arylamide Ugi-Smiles adducts or N-arylepoxyisoindolines, products of tandem Ugi-Smiles Diels-Alder cyclizations, in moderate yields. A thienyl-substituted aldehyde was also a competent component for Ugi-Smiles adduct formation.
Keywords: Diels–Alder cycloaddition; Ugi–Smiles coupling; epoxyisoindoline; multicomponent coupling reaction; tandem reaction.